ES364633A1 - Dibenzazepine acetic acid derivatives - Google Patents
Dibenzazepine acetic acid derivativesInfo
- Publication number
- ES364633A1 ES364633A1 ES364633A ES364633A ES364633A1 ES 364633 A1 ES364633 A1 ES 364633A1 ES 364633 A ES364633 A ES 364633A ES 364633 A ES364633 A ES 364633A ES 364633 A1 ES364633 A1 ES 364633A1
- Authority
- ES
- Spain
- Prior art keywords
- methyl
- acetyl
- chloro
- benzyl
- formyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
- C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
- C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
- C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K31/00—Medicinal preparations containing organic active ingredients
- A61K31/33—Heterocyclic compounds
- A61K31/395—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins
- A61K31/55—Heterocyclic compounds having nitrogen as a ring hetero atom, e.g. guanethidine or rifamycins having seven-membered rings, e.g. azelastine, pentylenetetrazole
-
- G—PHYSICS
- G01—MEASURING; TESTING
- G01M—TESTING STATIC OR DYNAMIC BALANCE OF MACHINES OR STRUCTURES; TESTING OF STRUCTURES OR APPARATUS, NOT OTHERWISE PROVIDED FOR
- G01M3/00—Investigating fluid-tightness of structures
- G01M3/02—Investigating fluid-tightness of structures by using fluid or vacuum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Public Health (AREA)
- Pharmacology & Pharmacy (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Veterinary Medicine (AREA)
- General Physics & Mathematics (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Other In-Based Heterocyclic Compounds (AREA)
- Cosmetics (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
Novel dibenzazepine derivatives of Formula (I) in which R 1 is hydrogen or C 1-3 alkyl, R 2 is hydrogen or C 1-4 alkyl and R 3 is hydrogen or chlorine, and their pharmaceutically acceptable salts with bases, are prepared by (a) subjecting a compound of Formula (II) in which R 2 1 is hydrogen, C 1-4 alkyl, C 1-4 alkanoyl or benzyl, to alcoholysis with a C 1-6 alkanol and hydrolysing the resulting alkyl ester, or (b) hydrolysing a compound of Formula (III) in which R 2 11 is hydrogen, C 1-4 alkyl or C 1-4 alkanoyl, and X is a group which can be hydrolysed to obtain a carboxyl group, e.g. a cyano, carboxylic acid imido ester, carboxylic acid ester or carbamoyl group, or a thiocarbamoyl group which can be mono- or di-alkyl substituted at the N-atom, whereby in the case of di-substitution, the two alkyl groups may be joined by way of an oxygen atom, or (c) hydrolysing a compound of Formula (IV) in which R 2 111 is C 1-4 alkanoyl, or (d) reacting a compound of Formula (V) in which R 4 1 is hydrogen, C 1-6 alkyl or benzyl, with a saturated solution of a hydrohalic acid at an elevated temperature, or (e) reacting a compound of Formula (V) in which R 4 1 is benzyl, with catalytically activated hydrogen, or (f) reacting a compound of Formula (VI) with a reactive ester of a C 1-4 alkanol, or (g) reacting a compound of Formula (VII) in which R 1 1 is C 1-3 alkyl, A 1 is cyano or C 2-6 (alkoxycarbonyl) and A 2 is C 2-6 (alkoxycarbonyl), C 3-7 (alkoxalyl), cyano or acetyl, with an alkali metal hydroxide in an organic or organic-aqueous medium or, if neither A 1 nor A 2 is cyano, also with an alkali metal alkanolate in an anhydrous medium or, if A 2 is not acetyl, also with a mineral acid in an organic-aqueous medium, and optionally in any of processes (a) to (g) liberating the carboxylic acid from a salt obtained and/or converting the obtained carboxylic acid into a pharmaceutically acceptable salt with a base. Intermediates and starting materials.-The following 10,11-dihydro-5H-dibenz[b,f]azepine compounds are prepared in the examples: 3- cyanomethyl - 5 - methyl -, 3- cyanomethyl- 5 - butyl -, 3 - (1 - cyanoethyl) - 5 - methyl-, 2 - cyanomethyl - 5 - benzyl -, 2 - cyanomethyl- 5 - methyl -, 2 - cyanomethyl - 5 - methyl- 7 - chloro -, 2 - cyano - 5 - methyl -, 3 - ethoxycarbonylmethyl - 5 - methyl -, 3 - (1 - ethoxycarbonyl - ethyl) - 5 - methyl -, 2 - ethoxycarbonylmethyl -, 3 - methoxycarbonyl -, 3 - (1 - methoxycarbonyl - ethyl) -, 3 - methoxycarbonylmethyl - 5 - methyl -, 3 - methoxycarbonylmethyl - 5 - butyl -, 2 - ethoxycarbonylmethyl - 5 - methyl -, 2 - (1 - ethoxycarbonyl - propyl) - 5 - methyl -, 2 - di - (ethoxycarbonyl)methyl -, 2 - [1,1 - di - (ethoxycarbonyl)ethyl] -, 2 - [1,1 - di - (ethoxycarbonyl)- propyl] -, 3 - carboxy - 5 - butyryl -, 3 - carboxy - 5 - acetyl -, 3 - (1 - carboxyethyl) - 5 - acetyl -, 3 - (1 - hydroxyethyl) - 5 - acetyl -, 3 - hydroxymethyl - 5 - acetyl -, 3 - hydroxymethyl - 5 - methyl -, 3 - hydroxymethyl - 5 - butyl -, 3 - (1 - hydroxyethyl) - 5 - methyl -, 2- hydroxymethyl - 5 - methyl -, 3 - hydroxymethyl - 5 - benzyl -, 3 - acetyl - 5 - butyryl-, 3 - acetyl - 5 - methyl -, 2 - acetyl - 5 - methyl-, 5 - benzyl -, 5 methyl-, 2 - formyl - 5 - methyl-, 2 - formyl - 5 - benzyl -, 3 - acetyl - 5 - formyl-, 3 - (1 - hydroxyethyl) - 5 - formyl -, 3 - carboxy- 5 - formyl -, 3 - methoxycarbonylmethyl - 5 - formyl -, 3 - (1 - methoxycarbonyl - ethyl)- 5 - formyl -, 2 - carbamoyl - 5 - methyl -, 3- carboxy - 5 - acetyl - 7 - chloro -, 3,5 - diacetyl- 7 - chloro -, 3 - hydroxymethyl - 5 - acetyl - 7 - chloro -, 3 - methoxycarbonyl - 5 - acetyl - 7 - chloro -, 3 - carboxymethyl - 5 - acetyl - 7 - chloro -, 2 - carboxymethyl - 5 - benzyl -, 3- methoxycarbonylmethyl - 5 - methyl -, 3,5- diacetyl - 7 - chloro -, 3 - chloro - 5 - acetyl-, 3 - bromomethyl - 5 - acetyl -, 3- (1 - bromoethyl) - 5 - acetyl -, 2 - hydroxymethyl - 3- chloro - 5 - methyl -, 2 - hydroxymethyl - 5 - methyl - 7 - chloro -, 2 - formyl - 3 - chloro - 5 - methyl -, 2 - formyl - 5 - methyl - 7 - chloro -, 2 - hydroxyliminomethyl - 5 - methyl -, 3 - (2- imino - 2 - ethoxy - 1 - ethyl) - 5 - methyl -, 3- bromomethyl - 5 - methyl -, 3 - bromomethyl- 5 - butyl -, 3- (1 - bromoethyl) - 5 - methyl-, 2 - bromomethyl - 5 - benzyl -, 2 - chloromethyl - 5 - benzyl -, 2 - chloromethyl - 5 - methyl -, 2 - chloromethyl - 5 - methyl - 7 chloro -, 3 - chloro - 5 - methyl-, 2 - or 3 - morpholinothiocarbonylmethyl - 5 - methyl -, 3 - morpholinothiocarbonylmethyl - 5 - acetyl-, 3 - cyanomethyl - 5 - acetyl -, 3- cyanomethyl- 5 - acetyl - 7 - chloro - and 3 - (1 - cyanoethyl). 5 - acetyl - 10,11 - dihydro - 5H - dibenz[b,f]- azepines. Pharmaceutical compositions having antiinflammatory, anti-oedematous, analgesic and anti-pyretic activity comprise, as active ingredient, one of the above novel compounds or salts, together with a pharmaceutical carrier. The compositions may be administered orally, parenterally, rectally or topically. The active compounds are also UV-absorbers and can be used in sun-protection oils and creams.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH305568A CH501635A (en) | 1968-02-29 | 1968-02-29 | Process for the preparation of new derivatives of 5H-dibenz (b, f) azepine |
Publications (1)
Publication Number | Publication Date |
---|---|
ES364633A1 true ES364633A1 (en) | 1971-02-01 |
Family
ID=4247593
Family Applications (5)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES364633A Expired ES364633A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364635A Expired ES364635A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364637A Expired ES364637A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364632A Expired ES364632A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364634A Expired ES364634A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
Family Applications After (4)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
ES364635A Expired ES364635A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364637A Expired ES364637A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364632A Expired ES364632A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
ES364634A Expired ES364634A1 (en) | 1968-02-29 | 1969-02-28 | Dibenzazepine acetic acid derivatives |
Country Status (13)
Country | Link |
---|---|
US (1) | US3624075A (en) |
JP (3) | JPS4927876B1 (en) |
AT (5) | AT286996B (en) |
BE (1) | BE729209A (en) |
BR (1) | BR6906750D0 (en) |
CH (5) | CH501639A (en) |
DE (2) | DE1965988A1 (en) |
DK (1) | DK122725B (en) |
ES (5) | ES364633A1 (en) |
FR (1) | FR2002897A1 (en) |
GB (1) | GB1259648A (en) |
IL (1) | IL31715A (en) |
NL (1) | NL6902779A (en) |
Families Citing this family (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4230703A (en) * | 1977-04-01 | 1980-10-28 | Teikoku Hormone Mfg. Co., Ltd. | 11-Oxodibenz(b,e)azepines |
US6468996B1 (en) * | 1998-10-21 | 2002-10-22 | Novo Nordisk A/S | Substituted hetero-polycyclic compounds as PPARα and PPARγ activators |
Family Cites Families (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH414643A (en) * | 1962-12-04 | 1966-06-15 | Geigy Ag J R | Process for the production of new azepine derivatives |
-
1968
- 1968-02-29 CH CH1281770A patent/CH501639A/en not_active IP Right Cessation
- 1968-02-29 CH CH305568A patent/CH501635A/en not_active IP Right Cessation
- 1968-02-29 CH CH1281870A patent/CH501640A/en not_active IP Right Cessation
- 1968-02-29 CH CH1281670A patent/CH501638A/en not_active IP Right Cessation
- 1968-02-29 CH CH1281570A patent/CH501637A/en not_active IP Right Cessation
-
1969
- 1969-02-21 NL NL6902779A patent/NL6902779A/xx unknown
- 1969-02-21 DK DK98269AA patent/DK122725B/en unknown
- 1969-02-24 US US801801A patent/US3624075A/en not_active Expired - Lifetime
- 1969-02-27 FR FR6905170A patent/FR2002897A1/fr not_active Withdrawn
- 1969-02-28 AT AT02014/70A patent/AT286996B/en not_active IP Right Cessation
- 1969-02-28 AT AT203869A patent/AT286994B/en not_active IP Right Cessation
- 1969-02-28 BE BE729209D patent/BE729209A/xx unknown
- 1969-02-28 ES ES364633A patent/ES364633A1/en not_active Expired
- 1969-02-28 IL IL31715A patent/IL31715A/en unknown
- 1969-02-28 ES ES364635A patent/ES364635A1/en not_active Expired
- 1969-02-28 ES ES364637A patent/ES364637A1/en not_active Expired
- 1969-02-28 AT AT201770A patent/AT286997B/en not_active IP Right Cessation
- 1969-02-28 BR BR206750/69A patent/BR6906750D0/en unknown
- 1969-02-28 DE DE19691965988 patent/DE1965988A1/en active Pending
- 1969-02-28 GB GB1259648D patent/GB1259648A/en not_active Expired
- 1969-02-28 AT AT201670A patent/AT289815B/en not_active IP Right Cessation
- 1969-02-28 DE DE19691910291 patent/DE1910291A1/en active Pending
- 1969-02-28 ES ES364632A patent/ES364632A1/en not_active Expired
- 1969-02-28 AT AT201570A patent/AT287729B/en not_active IP Right Cessation
- 1969-02-28 JP JP44014996A patent/JPS4927876B1/ja active Pending
- 1969-02-28 ES ES364634A patent/ES364634A1/en not_active Expired
-
1971
- 1971-07-02 JP JP46048717A patent/JPS4929197B1/ja active Pending
- 1971-07-02 JP JP46048716A patent/JPS4929196B1/ja active Pending
Also Published As
Publication number | Publication date |
---|---|
JPS4929197B1 (en) | 1974-08-01 |
GB1259648A (en) | 1972-01-05 |
US3624075A (en) | 1971-11-30 |
AT287729B (en) | 1971-02-10 |
AT286997B (en) | 1971-01-11 |
ES364634A1 (en) | 1971-02-01 |
DE1965988A1 (en) | 1970-11-19 |
CH501635A (en) | 1971-01-15 |
JPS4929196B1 (en) | 1974-08-01 |
ES364635A1 (en) | 1971-02-01 |
JPS4927876B1 (en) | 1974-07-22 |
CH501637A (en) | 1971-01-15 |
AT289815B (en) | 1971-05-10 |
CH501639A (en) | 1971-01-15 |
ES364637A1 (en) | 1971-02-01 |
CH501640A (en) | 1971-01-15 |
ES364632A1 (en) | 1971-02-01 |
NL6902779A (en) | 1969-09-02 |
IL31715A (en) | 1972-01-27 |
BR6906750D0 (en) | 1973-04-19 |
IL31715A0 (en) | 1969-04-30 |
BE729209A (en) | 1969-08-28 |
DE1910291A1 (en) | 1969-11-06 |
AT286994B (en) | 1971-01-11 |
CH501638A (en) | 1971-01-15 |
AT286996B (en) | 1971-01-11 |
FR2002897A1 (en) | 1969-10-31 |
DK122725B (en) | 1972-04-04 |
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